US6274732B1 - Process for the preparation of 1-[(cyclopent-3-en-1-yl)-methyl]-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione - Google Patents
Process for the preparation of 1-[(cyclopent-3-en-1-yl)-methyl]-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione Download PDFInfo
- Publication number
- US6274732B1 US6274732B1 US09/472,978 US47297899A US6274732B1 US 6274732 B1 US6274732 B1 US 6274732B1 US 47297899 A US47297899 A US 47297899A US 6274732 B1 US6274732 B1 US 6274732B1
- Authority
- US
- United States
- Prior art keywords
- compound
- formula
- process according
- preparation
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- KTTMTEPMCHIITQ-UHFFFAOYSA-M CCC1=C(C(=O)C2=CC(C)=CC(C)=C2)N(CC2CC=CC2)C(=O)NC1=O.CCC1=C(C(C#N)C2=CC(C)=CC(C)=C2)NC(=O)NC1=O.CCC1CC=CC1.[V]I Chemical compound CCC1=C(C(=O)C2=CC(C)=CC(C)=C2)N(CC2CC=CC2)C(=O)NC1=O.CCC1=C(C(C#N)C2=CC(C)=CC(C)=C2)NC(=O)NC1=O.CCC1CC=CC1.[V]I KTTMTEPMCHIITQ-UHFFFAOYSA-M 0.000 description 3
- GROKISNOEZWPDK-UHFFFAOYSA-N CCC1=C(C(C#N)C2=CC(C)=CC(C)=C2)NC(=O)NC1=O Chemical compound CCC1=C(C(C#N)C2=CC(C)=CC(C)=C2)NC(=O)NC1=O GROKISNOEZWPDK-UHFFFAOYSA-N 0.000 description 2
- BEMROAADXJFLBI-UHFFFAOYSA-N CCC1=C(C(=O)C2=CC(C)=CC(C)=C2)N(CC2CC=CC2)C(=O)NC1=O Chemical compound CCC1=C(C(=O)C2=CC(C)=CC(C)=C2)N(CC2CC=CC2)C(=O)NC1=O BEMROAADXJFLBI-UHFFFAOYSA-N 0.000 description 1
- FHZZFRGFOAUXGP-UHFFFAOYSA-N CCC1=C(C(=O)C2=CC(C)=CC(C)=C2)N(CC2CC=CC2)C(=O)NC1=O.CCC1=C(C(=O)C2=CC(C)=CC(C)=C2)NC(=O)NC1=O.CCC1CC=CC1.II Chemical compound CCC1=C(C(=O)C2=CC(C)=CC(C)=C2)N(CC2CC=CC2)C(=O)NC1=O.CCC1=C(C(=O)C2=CC(C)=CC(C)=C2)NC(=O)NC1=O.CCC1CC=CC1.II FHZZFRGFOAUXGP-UHFFFAOYSA-N 0.000 description 1
- ULZGEHFFLIZCQN-UHFFFAOYSA-M CCC1=C(C(C#N)C2=CC(C)=CC(C)=C2)NC(=O)NC1=O.CCC1=C(OC)N=C(OC)N=C1C(C#N)C1=CC(C)=CC(C)=C1.[V].[V]I Chemical compound CCC1=C(C(C#N)C2=CC(C)=CC(C)=C2)NC(=O)NC1=O.CCC1=C(OC)N=C(OC)N=C1C(C#N)C1=CC(C)=CC(C)=C1.[V].[V]I ULZGEHFFLIZCQN-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
Definitions
- the present invention relates to a process for the preparation of a compound of the general formula (I) and a novel reactant useful for the process.
- the inventors have developed the compound of the formula (I) useful as an antivirus agent, especially for the treatment of AIDS (Korean patent application, No. 96-47458; PCT/KR96/00265).
- the compound of the formula (I) may be prepared by reacting a compound of the formula (II) with a compound of the formula (III).
- the reaction may be represented by the following scheme (1).
- Lie is a leaving group such as halogen atom, alkylsulfonyl, or arylsulfonyl.
- the inventors have continued their efforts to improve the process for the preparation of the compound of the formula (I), and now found a novel reactant useful for the process. As the result, a simpler and more economic process for the preparation of the compound can be established by using the novel reactant.
- an object of the invention is to provide a simple and economic process for the preparation of the compound of the formula (I).
- Another object of the invention is to provide a new reactant which is useful for the process for the preparation of the compound of the formula (I).
- the process according to the present invention simplifies the synthesis and increases the yield of the objective compound, and may be represented by the following scheme (2).
- Lie is a leaving group such as halogen atom, alkylsulfonyl, or arylsulfonyl.
- the compound of the formula (I) may be prepared by reacting a compound of the formula (IV) with a compound of the formula (III) in the presence of a base with injection of oxygen.
- the bases used in the above reaction may include, for example, sodium bicarbonate, sodium carbonate, potassium carbonate and sodium hydride.
- the solvents used in the reaction may include organic polar solvents such as dimethylformamide.
- the catalysts such as lithium iodide, sodium iodide and potassium iodide may be used in the reaction.
- the reaction may be carried out at the temperature of 10 ⁇ 100° C. for 4-72 hours.
- the new reacting compound of the formula (IV) of the invention may be prepared by the following reaction scheme (3).
- the compound of the formula (IV) may be prepared by hydrolyzing a compound of the formula (V) in the presence of an acid.
- the starting material of the formula (V) may be prepared by various known methods.
- Acids used in the reaction may include, for example, hydrochloric acid and sulfuric acid.
- the reaction may be carried out at the temperature of 25 ⁇ 120° C. for 1-48 hrs.
- the present invention provides an improved process for the preparation of the compound of the formula (I), which is useful as an antivirus agent, with features of simple process and increased yield.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR99-7892 | 1999-03-10 | ||
| KR1019990007892A KR100311949B1 (ko) | 1999-03-10 | 1999-03-10 | 1-[(사이클로펜트-3-엔-1-일)메틸]-5-에틸-6-(3,5-다이메틸벤조일)-2,4-피리미딘다이온의제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US6274732B1 true US6274732B1 (en) | 2001-08-14 |
Family
ID=19576087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/472,978 Expired - Lifetime US6274732B1 (en) | 1999-03-10 | 1999-12-28 | Process for the preparation of 1-[(cyclopent-3-en-1-yl)-methyl]-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6274732B1 (ko) |
| EP (1) | EP1035116B1 (ko) |
| JP (1) | JP3272340B2 (ko) |
| KR (1) | KR100311949B1 (ko) |
| DE (1) | DE69914719T2 (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060094738A1 (en) * | 2004-08-20 | 2006-05-04 | Buck Institute For Age Research | Small molecules that replace or agonize p53 function |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5922727A (en) | 1996-02-22 | 1999-07-13 | Samjin Pharmaceutical Co., Ltd | Antiviral substituted pyrimidinedione homocarbocyclic nucleoside derivatives and methods for the preparation thereof and compositions containing the same as active ingredients |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0151811B1 (ko) * | 1993-12-21 | 1998-10-15 | 강박광 | 신규한 항바이러스성 2,4-피리미딘디온 유도체 및 그의 제조방법 |
| KR100219922B1 (ko) * | 1996-05-16 | 1999-09-01 | 이서봉 | 신규한 항바이러스성 6-아릴옥시 및 6-아릴카르보닐 2,4-피리미딘디온 유도체 및 그의 제조 방법 |
-
1999
- 1999-03-10 KR KR1019990007892A patent/KR100311949B1/ko not_active IP Right Cessation
- 1999-11-25 DE DE69914719T patent/DE69914719T2/de not_active Expired - Lifetime
- 1999-11-25 EP EP99123517A patent/EP1035116B1/en not_active Expired - Lifetime
- 1999-12-28 US US09/472,978 patent/US6274732B1/en not_active Expired - Lifetime
-
2000
- 2000-03-09 JP JP2000065578A patent/JP3272340B2/ja not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5922727A (en) | 1996-02-22 | 1999-07-13 | Samjin Pharmaceutical Co., Ltd | Antiviral substituted pyrimidinedione homocarbocyclic nucleoside derivatives and methods for the preparation thereof and compositions containing the same as active ingredients |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060094738A1 (en) * | 2004-08-20 | 2006-05-04 | Buck Institute For Age Research | Small molecules that replace or agonize p53 function |
| US7994184B2 (en) * | 2004-08-20 | 2011-08-09 | Buck Institute | Small molecules that replace or agonize p53 function |
| US9789121B2 (en) | 2004-08-20 | 2017-10-17 | Buck Institute | Small molecules that replace or agonize p53 function |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1035116B1 (en) | 2004-02-11 |
| JP2000264878A (ja) | 2000-09-26 |
| JP3272340B2 (ja) | 2002-04-08 |
| DE69914719D1 (de) | 2004-03-18 |
| KR100311949B1 (ko) | 2001-11-02 |
| EP1035116A1 (en) | 2000-09-13 |
| KR20000059946A (ko) | 2000-10-16 |
| DE69914719T2 (de) | 2004-07-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH09316072A (ja) | パロキセチンの製造方法 | |
| CN112062712A (zh) | 一种2-（5-溴-3-甲基吡啶-2-基）乙酸盐酸盐的制备方法 | |
| JPH0776209B2 (ja) | 光学活性３―ヒドロキシピロリジン誘導体の製造方法 | |
| EP0001500A1 (en) | 1-Carbocyclic aryl-2-mono or -bis(alkoxycarbonyl) guanidino ethanes, and methods for their preparation and the preparation therefrom of 4,5-dihydro-2-alkoxycarbonylamino-5-carbocyclic aryl imidazoles | |
| US6274732B1 (en) | Process for the preparation of 1-[(cyclopent-3-en-1-yl)-methyl]-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione | |
| JP4922152B2 (ja) | フッ素化プロリン誘導体の製造方法 | |
| KR20080031910A (ko) | １-[시아노(４-하이드록시페닐)메틸]사이클로헥사놀화합물의 제조 방법 | |
| US20060247437A1 (en) | Preparation of ketone amides | |
| KR100369274B1 (ko) | 4-히드록시-2-피롤리돈의개량제법 | |
| JP2578797B2 (ja) | Ｎ−（スルホニルメチル）ホルムアミド類の製造法 | |
| JPH0386873A (ja) | １，３―ジオキソランケトンの製法 | |
| CN115433133B (zh) | 一种l-肌肽的合成方法 | |
| JPH11171876A (ja) | ２，４−オキサゾリジンジオン類の製造方法 | |
| WO2023100110A1 (en) | Process for preparing brivaracetam | |
| JP3518627B2 (ja) | 光学活性５−ヒドロキシメチルオキサゾリジノン誘導体の製造法 | |
| KR101962516B1 (ko) | 시타글립틴 제조용 중간체 화합물, 이의 제조방법 및 이를 이용한 시타글립틴 화합물의 제조 방법 | |
| JP2734646B2 (ja) | ２，２―ジフルオロカルボン酸誘導体の新規合成法 | |
| JP3818785B2 (ja) | α，β−ジカルボニル化化合物のための製造方法 | |
| JPH07267950A (ja) | ５−クロロ−ｎ−（４，５−ジヒドロ−１ｈ−イミダゾール−２−イル）−２，１，３−ベンゾチアジアゾール−４−アミン又はその酸付加塩の製造方法 | |
| US6506907B1 (en) | Process | |
| JPH07316137A (ja) | （ヘキサヒドロ−１−メチル−１ｈ−アゼピン−４−イル）−ヒドラジン又はその塩の製造方法 | |
| JP3013760B2 (ja) | ４−ヒドロキシ−２−ピロリドンの製法 | |
| CN117886725A (zh) | 一种阿普斯特中间体的制备工艺 | |
| CN111662233A (zh) | 一种一步法合成4-氯-1h-咪唑-2-羧酸乙酯的方法 | |
| PL150350B1 (en) | Method of obtaining 1-3-bromo-/2s/-methylpropionyl -pyrrolidine-/2s/-carboxylic acid of formula 1 and its monohydride |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: SAMJIN PHARMACEUTICAL CO., LTD., KOREA, REPUBLIC O Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHO, EUI-HWAN;CHUNG, SUN-GAN;LEE, SUN-HWAN;AND OTHERS;REEL/FRAME:010493/0230 Effective date: 19991209 |
|
| AS | Assignment |
Owner name: SAMJIN PHARMACEUTICAL CO., LTD., KOREA, REPUBLIC Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHO, EUI-HWAN;CHUNG, SUN-GAN;LEE, SUN-HWAN;AND OTHERS;REEL/FRAME:010706/0495 Effective date: 19991209 |
|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
| FPAY | Fee payment |
Year of fee payment: 4 |
|
| FPAY | Fee payment |
Year of fee payment: 8 |
|
| FPAY | Fee payment |
Year of fee payment: 12 |
|
| SULP | Surcharge for late payment |
Year of fee payment: 11 |